The CEO skill that transformed my business … and my life

Years ago, I was sitting with the executive coach specifically tasked with helping me transition into my brand new CEO role.

As I was relaying the events of my week, I paused, sighed heavily, rolled my eyes, and exclaimed, “Oh! And we finally got everyone to show up on time for a meeting.” 

My team, extremely competent and committed, had differing ideas of what “on time” meant. However, from my vantage point I could see how the scattered start times were affecting the company’s work flow as a whole….plus tardiness really annoys me…. so I had made it my mission to shift the collective behavior. And it was taking much longer than I had hoped.

As I started back in on my list of “important” updates, my coach interrupted me.

“Lisa,” she said. “That’s a win! Do you see that?” 

I did not. 

It did not feel like a win. It felt like something that shouldn’t have been an issue in the first place. It felt like I wanted to be focusing on other things. It felt like we were progressing more slowly than I had hoped. 

It felt like a win in the same way getting my car repaired after getting rear ended felt - time consuming, annoying, non-optional, and somehow my problem even though I didn’t cause it.

My coach, highly perceptive to my distinctive sneer, continued.

“If you’re going to be a CEO, you’re going to have to learn to celebrate the small wins.”

I whined back dismissively, “Yeah, I suppose…”

“No,” she stated firmly. “The small wins are important, because as a CEO, they’re the only ones you will get.”

This statement hit me like a ton of bricks to the gut.

“I want my money back,” I exclaimed.

She was right. Here’s why.

If a CEO is doing their job, they are maintaining a high level of perspective. They are seeing it all.

They are aware of every effort, every struggle, and every obstacle that went into each win. They also see the future work that needs to be planned and executed as a result of each win. 

When a CEO maintains perspective, every win - especially the large ones - carries inherent baggage. As they say - more money, more problems. And it’s the CEO’s job to both make more money and also lead their team through solving the problems that occur.

When the landscape is complicated and everything feels loaded - celebrating the small wins is crucial. Celebrating the small wins is a life line. Celebrating the small wins showcases the rocks that make hopping across a wide river possible. 

And plus, celebrating the small wins gives true perspective. It completes the picture - painting in the positive with the negative, the past in with the future. And whether or not you’re a CEO, perspective is incredibly valuable - especially during times of complication and uncertainty. 

At first, I was terrible at celebrating the small wins.

Committed to maintaining a realistic (read pessimistic) viewpoint, and not so great with the “touchy feely” stuff, it felt like an uncomfortable, mind-numbing, and pointless exercise.

I would sit down each day to make my coach-imposed list of my three small wins from the day before and slowly, routinely, and begrudgingly cultivated the mindfulness necessary to notice the wins as they happened.

Somewhere along the way, I became a stronger leader. I started noticing my team’s wins more and had the awareness and skills to acknowledge them. I started taking things less personally and felt more in control.

Our business thrived. And I became a happier, less stressed out person.

I hadn’t realized exactly how far I had come until years, when I was sitting in front of a new CEO. She was telling me about a step she had made in shifting her company culture. I interrupted her.

“That’s a win! Do you see that?” I asked.

She did not.

Without thinking twice, I advised, “If you’re going to be a CEO, you’re going to have to learn to celebrate the small wins… they’re the only ones you will get.” 

She rolled her eyes.

I laughed. She had no idea how much she was about to grow as a leader - but I did!

One final thing.

I’m no longer the CEO of that company, but I am a business owner and a human being. 

And celebrating the small wins continues to be instrumental to my growth and peace. 

Remember that whole thing about perspective? Perspective is an anchor in times of uncertainty and change. Perspective gives us a pole to climb up when the emotional flood waters start rolling in. 

Celebrating the small wins is one of the quickest ways to develop higher perspective. Yes, it may feel uncomfortable. Yes, it may feel like you’re just going through the motions at first. 

However, if you start writing down just three small wins every day, you will eventually start to notice a deeper sense of control and happiness. 

And before you know it, someone will be complaining to you and you will interrupt them.

“Hey, that’s a win! Do you see that?” you’ll ask.

They will not. And you will see how far you’ve come.